Manufacture of substituted sulphur dyestuffs in substance or on the fiber



Patented Aug. 23, 1932 FJFIQCRE RI-IINE, AND LUDWIG ZEH, F WIESDORF-ON-THE-RI-IINE, GERMANY, 'ASS IGNORS' TO GENERAL ANILINE WORKS, ING., OF NEW YORK, N. Y., A CORPOEATION 'QF DELA- WARE MANUFACTURE OF SUBSTITUTED SULPHUR EYEST UFFS IN FIBER No Drawing. Application filed October 14, 1929, Serial No. 399,707, and in Germany August 31, 1927- The present invention relates to new substituted sulphur dyestuffs produced on the fiber and to the fiber dyed therewith.

For the production of ouinew dyestuffs we use as starting materials the sulphur dyestuffs which are obtainable by reacting upon ,B-dinaphthol of the formula:

with a sulphurating agent, such as sulphur, a

sulphur halogenide and mixtures of sulphur agents are, for instance, described in the U. S.

Patent No. 688,999, namely ethyl bromide,

benzyl chloride, dimethyl surfate, dimethylbenzylphenyl ammonium chloride, and the like.

We prefer to carry out the process by dyeing vegetable fibers with the above mentioned starting materials, rinsing the dyed goods and boiling them with a solution of the alkylating or aralkylating agent, for instance, with a solution of dimethylbenzylphenyl ammonium chloride, and preferably in the presence of an agent capable of exerting a, reducing action andof a small amount of alkali. By working at a lower temperature or without the addition of a reducing agent the development is retarded and it may, according to the agents used in the subsequent treatment, entirely fail to take place. The dyeings obtained display very satisfactory fastness to boiling and kier boiling.

Our new dyestufis yield clear red shades of a quality which was not obtainable hitherto by means of sulphur dyestuifs.

The following example illustrates the invention:--

EmampZe.The dyeing obtained on cotton withthe sulphur dyestuft', produced from ,8- dinaphthol by heating the same with sulphur monochloride to 100 C. and afterwards, when the vigorous reaction has subsided, at about 250260 C. for about 4 hours (compare Example 1 of the U. S. Patent No. 1,7 59,- 264) is equeezed and rinsed and then treated for 1020 minutes in a boiling bath, containing 4 cc. of caustic soda lye (40 1%.), 1.5 grams of hydro-sulfite and 10 grams of dimethylbenzylphenyl-ammonium chloride per litre. A red dyeing is obtained of excellent fastness to boiling. I

By treating in the same manner the dyestuff obtainable by heating B-dinaphthol with a mixture of sulphur monochloride and sulphur to to 100 C. and afterwards at 250 to 260 C. for several hours (compare Example 2 of U. S. Patent No. 1,759,264), a brick red is obtained.

This application is acontinuation-in-part of our co-pending application Ser. No. 287 342, filed on June 21st, 1928.

We claim:

1. As new products the sulphur dyestufis which are obtainable by treating a sulphur dyestufii, obtainable by sulphuration of ,8 dinaphthol, with a compounds of the group consisting of alkylating and aralkylating agents, in the presence of a small amount of alkali and an agent capable of exerting a reducing action, the said dyestuffs yielding clear red shades.

2. As new products the sulphur dyestuffs which are obtainable by treating a sulphur dyestufl, obtainable by sulphuration of ,8- dinaphhol, with dimethylbenzylphenyl ammonium chloride, in the presence of a small amount of alkali. and an agent capable of exerting a reducing action, the said dyestuffs yielding clear red shades.

8. As a new product the sulphur dyestufl' which is obtainable by treating a sulphur dyestuff, obtainable by heating ,8-dinaphthol with sulphur monochloride to 60100 C. and afterwards at 250260 C. for about 4 hours,

with dimethylbenzylphenyl ammonium chlo- SUBSTANCE on on H ride, in the presence of a small amount of alkali and sodium hydrosulfite, the said dyestulf yielding a clear red shade of excellent fastness .jto Zboiling.

4. Vegetable fibers dyed with a sulphur dyestuff claimed in claim 1.

SE-Vegetable:fibers dyed with a sulphur dyestufi' claimed in claim 2. a V Vegetahlefibers dyed with the sulphur dyestufi' claimed in claim 3.

In testimony whereof We allix our signama s; r ERWIN KRAMER.

BERNHARD BOLLWEG. LUIDWIG Z'EH. 

